Pal-Glu(OSu)-OMe
[CAS# 294855-90-6]

Identification

• Classification: Biochemical >> Common amino acids and protein drugs
• Name: Pal-Glu(OSu)-OMe
• Synonyms: 5-O-(2,5-dioxopyrrolidin-1-yl) 1-O-methyl 2-(hexadecanoylamino)pentanedioate
• Molecular Formula: C₂₆H₄₄N₂O₇
• Molecular Weight: 496.64
• Protein Sequence: X
• CAS Registry Number: 294855-90-6
• SMILES: CCCCCCCCCCCCCCCC(=O)NC(CCC(=O)ON1C(=O)CCC1=O)C(=O)OC

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.503, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

Pal-Glu(OSu)-OMe is a synthetic derivative used in peptide modification, particularly in lipidation processes that enhance the properties of peptides and proteins for therapeutic applications. The structure of this compound includes a palmitoyl (Pal) group, which is a long-chain fatty acid, attached to the amino acid glutamate (Glu). The (OSu) component refers to the N-hydroxysuccinimide (NHS) ester, which is a commonly used functional group that facilitates the attachment of molecules to amine groups through nucleophilic substitution. The (OMe) at the end indicates the presence of a methoxy group, which can influence the compound’s solubility and reactivity.

The discovery of Pal-Glu(OSu)-OMe and similar compounds is tied to the exploration of lipid-modified peptides, particularly in the field of drug delivery and protein engineering. Lipidation, the process of attaching fatty acids like palmitic acid to peptides, has been recognized as a method to increase the hydrophobicity of peptides, enhancing their interaction with cellular membranes and improving their pharmacokinetic properties, such as stability, half-life, and bioavailability.

The key feature of Pal-Glu(OSu)-OMe lies in the NHS ester group, which reacts efficiently with primary amine groups under mild conditions. This property makes the compound highly valuable for modifying peptides and proteins in both research and industrial settings. It enables the covalent attachment of the palmitoyl group to peptide sequences, which in turn enhances their ability to anchor to cell membranes, making them more effective as therapeutic agents or molecular probes.

In practical applications, Pal-Glu(OSu)-OMe is commonly used in the synthesis of lipidated peptides that are involved in drug delivery systems. For instance, palmitoylated peptides have been shown to improve the delivery of peptide-based drugs across cellular membranes, making them more effective in targeting specific tissues or cells. This modification is particularly useful for peptides that might otherwise be rapidly degraded in biological environments.

Additionally, lipidated peptides synthesized using compounds like Pal-Glu(OSu)-OMe are utilized in vaccine development. Lipidation can enhance the immunogenicity of peptide antigens by promoting stronger interactions with immune cells, ultimately leading to a more robust immune response. This has implications for the development of vaccines targeting a wide range of diseases, including viral infections and cancer.

Another important application of Pal-Glu(OSu)-OMe is in the study of membrane proteins. By attaching palmitoyl groups to peptides that mimic or interact with membrane-bound proteins, researchers can study the behavior of these proteins in their native lipid environments, gaining insights into their function and role in diseases.

Overall, Pal-Glu(OSu)-OMe is an important tool in both basic research and pharmaceutical development, particularly in the fields of peptide drug delivery, vaccine design, and membrane protein studies. Its ability to facilitate the attachment of hydrophobic fatty acid chains to peptides and proteins opens up new possibilities for enhancing the therapeutic potential of these biomolecules.

References

none